WO1998017664A1 - Derives de dioxane, compositions de cristaux liquides contenant ces derives, et dispositif d'affichage a cristaux liquides fabrique a partir de ces derniers - Google Patents

Derives de dioxane, compositions de cristaux liquides contenant ces derives, et dispositif d'affichage a cristaux liquides fabrique a partir de ces derniers Download PDF

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WO1998017664A1
WO1998017664A1 PCT/JP1997/002257 JP9702257W WO9817664A1 WO 1998017664 A1 WO1998017664 A1 WO 1998017664A1 JP 9702257 W JP9702257 W JP 9702257W WO 9817664 A1 WO9817664 A1 WO 9817664A1
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compound
atom
liquid crystal
group
hhb
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PCT/JP1997/002257
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English (en)
Japanese (ja)
Inventor
Yasuhiro Haseba
Tomoyuki Kondou
Shuichi Matsui
Kazutoshi Miyazawa
Hiroyuki Takeuchi
Yasusuke Hisatsune
Fusayuki Takeshita
Etsuo Nakagawa
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Chisso Corporation
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Priority to EP97928518.6A priority Critical patent/EP0881221B1/fr
Priority to JP51919698A priority patent/JP4782255B2/ja
Priority to AU32768/97A priority patent/AU3276897A/en
Priority to US09/101,999 priority patent/US6235355B1/en
Publication of WO1998017664A1 publication Critical patent/WO1998017664A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
    • C09K19/406—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals containing silicon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Definitions

  • Dioxane derivative liquid crystal composition containing the same, and
  • the present invention relates to a liquid crystal compound effective as a component of a liquid crystal composition, particularly a dioxane derivative suitable for use as a component of a liquid crystal composition for TFT, a liquid crystal composition containing the same, and a liquid crystal composition containing the same.
  • the present invention relates to a configured liquid crystal display device.
  • a liquid crystal display device uses the optical anisotropy and dielectric anisotropy of a liquid crystal material.
  • Force ⁇ depending on the display method, TN type (twisted nematic type), DS type (dynamic scattering type), G.
  • TN type twisted nematic type
  • DS type dynamic scattering type
  • G G
  • H type guest's host type
  • DAP type alignment phase change type
  • STN type super twisted nematic type
  • the liquid crystal material used in any display element must be stable to moisture, air, heat, light, etc., exhibit a liquid crystal phase over as wide a temperature range as possible around room temperature, and have low viscosity. It has good compatibility with liquid crystal compounds and liquid crystal compounds, has a large dielectric anisotropy value (A s), has an optimum refractive index anisotropy value ( ⁇ ⁇ ), and is chemically and electrically stable Must. In particular, a high voltage holding ratio is required for an active matrix type display element represented by a TFT type. At present, no single compound satisfies all of these conditions, and a liquid crystal composition obtained by mixing several types of liquid crystal compounds and liquid crystal compounds is used. is the current situation.
  • Patent Publication No. 01-044966 discloses a compound (10) of the following formula.
  • the compound (10) has a higher voltage holding ratio than a liquid crystal compound having a cyano group, and is therefore mainly used as a component of a liquid crystal composition for TFT.
  • the extrapolation As (extrapolation) of the compound (10) dissolves the compound (10) in a mother liquid crystal having a nematic phase, and the value of ⁇ of the composition and ⁇ Is the compound (10) calculated from the values and the mixing ratio, and the following ⁇ indicates this extrapolation ⁇ .) Is as small as 8.5. It cannot be used as a representative liquid crystal material for low voltage driving.
  • the compound (11) has a value of 11.0, which is larger than that of the compound (10), but is still inadequate and is not a material that can meet the demand for lowering the voltage of the market as described above.
  • Published Patent Application No. 04-5066361 discloses a trifluoromethylphenyl derivative (12) and a trifluoromethoxyphenyl derivative (13).
  • ⁇ ⁇ of these compounds still cannot meet the demand for lowering the voltage of the market as in the case of the compounds (10) and (11).
  • ⁇ of (for example, compound U 3) is about 5 (I DY (Television Technical Report) 95).
  • a dioxane derivative represented by the following formula (14) is disclosed in Japanese Patent Laid-Open Publication No. H02-233336.
  • This compound has a large ⁇ of 15.7, but it is impossible to sufficiently reduce the driving voltage to the required level with this size, and furthermore, a fluorine-based liquid crystal compound that does not have a conventional dioxane ring Therefore, the voltage holding ratio is lower than that of the above, and a large ratio cannot be included in a material for a liquid crystal display element which requires a high voltage holding ratio.
  • the voltage holding ratio of the compound (11) is 98% at 25 ° C and 96% at 100
  • the voltage holding ratio of the compound (14) is 25 ° C at 25 ° C. They are 98% and 92% at 100 ° C.
  • the present inventors have studied diligently, and found that a liquid crystalline compound having an SP 3 carbon bonded to the 2-position of a 3-dioxane 2,5-diyl group and having a fluorine-based or chlorine-based electron-withdrawing group at the molecular terminal is obtained.
  • the inventors have found that they have a specific large ⁇ s, a high voltage holding ratio, and are most suitable as a liquid crystal material for TFT low voltage driving represented by 2.5 V driving, and have completed the invention.
  • An object of the present invention is to provide a liquid crystal material for a low voltage drive TFT type liquid crystal display element having a remarkably large ⁇ s value, a high voltage holding ratio, and a good compatibility with existing liquid crystal compounds.
  • An object of the present invention is to provide a liquid crystal composition that combines the above, and a liquid crystal display device configured using the same.
  • R represents an alkyl group having 1 to 20 carbon atoms or a hydrogen atom
  • n 1 and n 2 are each independently an integer from 0 to 2, and n 1 + n 2 ⁇ 2
  • Q, and Q 2 each independently represent a hydrogen atom or a fluorine atom,, represents a chlorine atom,
  • A indicates (a), (b) or (c),
  • ⁇ AO and A 1 represent a 1,4-cyclohexylene group or a 1,4-phenylene group in which one or more hydrogen atoms may be replaced by a fluorine atom or a chlorine atom, but A, ring A 0 And one or two carbon atoms in the 1,4-cyclohexylene group in ring A 1 may be substituted with a gayne atom,
  • Z a and Z b are independently a single bond, respectively, - CH 2 CH 2 -, one CH 2 CH 2 CH 2 CH 2 -, One ⁇ _CH 2 - one CH 2 ⁇ one one C_ ⁇ _ ⁇ mono- or One CF 20 —
  • Y represents a hydrogen atom, a halogen atom, or a halogenated alkyl group having 1 to 5 carbon atoms, and one or more non-adjacent methylene groups in the group may be substituted with an oxygen atom or a sulfur atom;
  • ring A 1 is strong, 1,4-phenylene and Z a and Z b are single bonds
  • Q and Q 2 represents a fluorine atom or a chlorine atom
  • Y is a fluorine atom or a chlorine atom
  • Q 2 Each is independently a fluorine atom or a chlorine atom.
  • A (c), or Z b is one CH 2 CH 2 CH 2 CH 2 —, or Za when n 1 is not 0 is —CH 2 CH 2 CH 2 CH 2 — (1)
  • a liquid crystal composition comprising at least one kind of the derivative according to any one of the above items (1) to (8).
  • 1 to 3 are alkyl groups having 1 to 10 carbon atoms.
  • any hydrogen atom may be replaced by a fluorine atom.
  • Is a fluorine atom, a chlorine atom, OCF 3 , OCF 2 H, CF 3 , CF 2 H, CFH 2 , ⁇ CF 2 CF 2 H Or ⁇ CF 2 C FHC F 3 , L and L 2 each independently represent a hydrogen atom or a fluorine atom, and Z!
  • ring B is xylene trans one 1, 4 Shikuro, 1, 3
  • ring C is trans-1,4-cyclohexylene or hydrogen Represents 1,4-phenylene in which the atom may be substituted by a fluorine atom, and in the compound of each formula, each atom constituting them may be substituted by an isotope thereof.
  • a liquid crystal composition comprising at least one selected compound.
  • Y 2 represents one CN or one C ⁇ C—CN
  • —Ring E represents trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-1,5 —
  • ring G represents trans-1,4-cyclohexylene, pyrimidine-1,2,5-diyl, or a hydrogen atom in which a hydrogen atom may be replaced by a fluorine atom
  • 4 represents 1-phenylene
  • ring H represents trans-1,4-cyclohexylene or 1,4-phenylene
  • Z 3 represents one CH 2 CH 2 —, one COO— or a single bond
  • L 3 , L 4 and L 5 each independently represent a hydrogen atom or a fluorine atom
  • b, c and d each independently represent 0 or 1
  • in the compound of each formula, each atom constituting them May be substituted with their isotopes.
  • a liquid crystal composition comprising
  • each element constituting them may be substituted with their isotope atom.
  • a liquid crystal composition comprising at least one compound selected from the group consisting of:
  • a liquid crystal composition comprising one type.
  • the general formula (2) It contains at least one compound selected from the compound group consisting of (3) and (4), and is selected from the compound group consisting of the general formulas (5) and (6) as the other part of the second component.
  • a liquid crystal composition comprising at least one compound and at least one compound selected from the group consisting of the general formulas (7), (8) and (9) as the third component. object.
  • liquid crystal composition according to any one of the above items (9) to (14), further comprising an optically active compound.
  • a liquid crystal display device comprising the liquid crystal composition according to any one of the above items (9) to (14).
  • a liquid crystal display device comprising the liquid crystal composition according to (15).
  • the compound represented by the general formula (1) of the present invention has a core of 3 to 5 rings including a dioxane ring, a force, a 2-position of the dioxane ring is bonded to the Sp 3 carbon, and It is a liquid crystalline compound having a fluorine-based or chlorine-based electron-withdrawing group at the end. With such a structure, a high voltage holding ratio and a specifically large voltage are obtained.
  • the compound of the present invention (No. 21) has the same alkyl chain and substituent of the terminal benzene ring as the compound (14), but has a specifically large ⁇ and a high voltage holding ratio as follows.
  • the voltage holding ratio of the compound (14) was 98% at 25 ° C. and 92% at 100 ° C., whereas the compound of the present invention (No. 21) was 25%. At 98% and 100 at 94%.
  • the compound (14) and the compound of the present invention (No. 21) should have approximately the same ⁇ ⁇ . It can be considered by those skilled in the art that the compound of the present invention (No. 21) has a ⁇ s 50% larger than that of the compound (14). This is a surprising and unexpected property.
  • the compound of the present invention specifically has a large ⁇ is shown below.
  • the compound (11) has ⁇ of 1 to 0, whereas the compounds (15) and (16), in which ethylene is introduced as a linking group, have a value of 9.7. Usually, ⁇ s is small.
  • the compound of the present invention (No. 98) is obtained.
  • the ⁇ of the compound (17) is 25.7.
  • that of the compound ( ⁇ 0.98) is surprisingly larger than that of the compound (17), 28.3.
  • Compounds having a Sp 3 carbon atom bonded to the 2-position of the dioxane ring and having a fluorine-based or chlorine-based electron withdrawing group at the molecular terminal have a high voltage holding ratio, It has a specifically large ⁇ .
  • the liquid crystal composition prepared using the compound represented by the general formula (1) of the present invention has a large voltage and a high voltage holding ratio, and is very useful for lowering the voltage of a TFT type liquid crystal display device. .
  • R is an alkyl group having 1 to 20 carbon atoms or a hydrogen atom.
  • the alkyl group preferably has 1 to 7 carbon atoms from the viewpoint of balance between viscosity and liquid crystal phase temperature range, and more preferably 2 to 5 carbon atoms.
  • the linking groups Za and Zb each independently represent a single bond, one CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, one CH 20 —, one OCH 2 —, one C 0 Alternatively Taking an CF 2 0- in which the force of each Toku ⁇ as follows.
  • linking groups Za and Zb are both single bonds have a relatively high clearing point, low viscosity, excellent compatibility with other liquid crystal compounds or liquid crystal compositions, and chemical and electrical properties. Stable. Compounds in which one of the linking groups Z a and Z b is a single bond and the other is one CH 2 CH 2 — are slightly inferior in viscosity but more excellent in compatibility than those in which both are single bonds. A compound in which at least one of a and Z b is one CH 2 CH 2 CH 2 CH 2 — is compared with a compound in which one of the linking groups Za and Z b is a single bond and the other is one CH 2 CH 2 —.
  • the compound is slightly inferior in viscosity but more excellent in compatibility, and a compound in which at least one of the linking groups Za and Zb is one CO 0- is more chemically and It has a somewhat poorer electrical stability but a larger ⁇ .
  • a compound in which at least one of the linking groups Za and Zb is —CF 20 — has low viscosity and is chemically and electrically stable.
  • terminal substituent Y The preferred structure of the terminal substituent Y and the characteristics of the compound having the substituent are shown below.
  • Compounds in which Y is fluorine have a relatively large ⁇ , have low viscosity, and have excellent compatibility with other liquid crystal compounds or liquid crystal compositions.
  • Compounds where ⁇ is CF 3 have a very large ⁇ .
  • Compounds in which ⁇ is OCF 3 or 0CF 2 H have low viscosity.
  • Y is C—OCF 2 CF 2 H, —OCF 2 C FHC F 3 have a large ⁇ and a high clearing point.
  • the compound of the present invention may have a fluorine or chlorine-substituted fuylene group
  • a compound having a larger number of fluorine or chlorine atoms in the lateral position of the fuylene group has a larger ⁇ ⁇ .
  • compounds having a small number thereof have a high clearing point and low viscosity.
  • Some of the compounds of the present invention have an 11-sila 1,4-cyclohexylene group and a 4-sila 1,4-cyclohexylene group.
  • the compounds having these groups in the present invention have a higher compatibility with other liquid crystal compounds and liquid crystal compositions at low temperatures than those having 1,4-cyclohexylene groups in the present invention. Excellent.
  • the compound of the present invention has a high voltage holding ratio and the above-mentioned characteristics due to its partial structure, but the compounds represented by the general formulas U-—) to (11S) have more preferable characteristics. .
  • the compound represented by the formula (1-B) is a compound represented by the general formula (1):
  • the compound represented by the formula (111) is represented by the general formula (1)
  • the compound represented by the formula (111) is a compound represented by the general formula (1)
  • the compound in which Z c 2 is a single bond is represented by the following general formula (1): 111 1 is 0,: 12 is 1, ring 1 is 1,4-cyclohexylene, Za is a single bond,
  • A is a compound wherein A is (a).
  • the compound in which Z c 2 is a single bond is represented by the general formula (1) in which n 1 is 1, n 2 is 0, ring A 0 is 1,4-cyclohexylene, and A is The compound is
  • the compound represented by the formula (1—H) is a compound represented by the general formula (1)
  • n 1 is 2, n 2 is 0, ring A 0 is 1,4-cyclohexylene, Za and Z b are A compound in which A is (b).
  • the compound represented by the formula (111) is a compound represented by the general formula (1)
  • the compound represented by the formula (111) is represented by the general formula (1)
  • n 1 and n 2 are both 1; ring A 0 is 1,4-cyclohexylene; ring A 1 is substituted or unsubstituted 1,4-phenylene; Za and Z b are each a single bond; ).
  • the compound represented by the formula (1-1K) is represented by the general formula (1)
  • ring A 1 is substituted or unsubstituted 1,4-phenylene,
  • n 1 and n 2 are both 0, Za and Z b are both single bonds, and k is (c).
  • n 1 is 0, n 2 is 1, ring A 1 is 4-cyclohexylene, Za and Z b are both single bonds, and A is (c).
  • Za is a single bond
  • Z b is —CH 2 CH 2 CH 2 CH 2 —
  • A is (a).
  • the compound represented by the formula (1-0) is a compound represented by the general formula (1):
  • the compound represented by the formula (1-1P) is represented by the general formula (1):
  • ring A 1 is substituted or unsubstituted 1,4-phenylene,
  • Z a is a single bond
  • Z b is one C00- or single CF 2 0-, a compound which is A Chikaraku (b).
  • n 2 is 1
  • ring A 1 is substituted or unsubstituted 1,4-olefin
  • Z a is a single bond
  • Z b is —COO— or one CF 20 —
  • the compound is A (a).
  • the compound represented by the formula (1—R) is a compound represented by the general formula (1):
  • R, Qi, Q 2 and Y are as defined above, Q 3 and Q 4 is a hydrogen atom or a fluorine atom independently of, respectively therewith, Z ci ⁇ Z c 3 are each a single bond or One CH 2 CH 2 —, and Z d indicates one CF 2 or one C.
  • the compounds of the general formulas (110), (111P) and (111S) in which Zd is -C00- are other compounds of the present invention.
  • the benzene ring is bonded to the 2-position of the conventional dioxane ring, and the voltage holding ratio is higher than that of the compound having a force and a single CO 0—.
  • All other compounds also have a high voltage holding ratio.
  • all of the compounds of the present invention have a specific large size, and thus can be driven at a low voltage.
  • the compound represented by the general formula (1-A) has a very low viscosity and very good compatibility. This compound is useful as a component of liquid crystal materials for high-speed response and liquid crystal materials that can be displayed even at low temperatures.
  • the compound represented by the general formula U- ⁇ ) has a high clearing point and low viscosity.
  • the compounds represented by the general formulas (1-C) and (1-D) have relatively high clearing points and are excellent in compatibility.
  • the compounds represented by the general formulas (1-B) to (1-D) are a group of compounds having a high clearing point, a good balance of viscosity and compatibility.
  • the compound represented by the general formula (11) has a relatively low viscosity and a large ⁇ . By using this compound, the value of ⁇ n of the liquid crystal composition can be easily adjusted to a required value, and low-voltage driving becomes possible.
  • the compounds represented by the general formulas (111) to (1-K) and (1-R) have high clearing points and large ⁇ . In particular, ⁇ of (1 ⁇ K) is very large. These compounds are also useful as components of liquid crystal materials that can be displayed at high temperatures.
  • All the compounds represented by the general formulas U-L) to (1-0) have a linking group of CH 2 CH 2 CH 2 CH 2 —, but this group of compounds is excellent in compatibility.
  • the compound of the present invention can facilitate low-voltage driving in a liquid crystal display element that requires a particularly high voltage holding ratio.
  • the compound of the present invention is a liquid crystal compound particularly suitable for a liquid crystal composition for TFT, but can be suitably used for other uses.
  • liquid crystal composition for TN liquid crystal composition for guest-host mode
  • liquid crystal composition for polymer dispersed liquid crystal display device liquid crystal composition for dynamic scattering mode
  • liquid crystal composition for STN ferroelectricity Liquid crystal composition
  • antiferroelectric liquid crystal composition liquid crystal composition for in-plane switching
  • the liquid crystal compound is a compound having a liquid crystal phase or a compound which does not impair the liquid crystal phase when mixed with another liquid crystal.
  • the liquid crystal composition of the present invention comprises at least one compound represented by the general formula U) of 0.1 to
  • the liquid crystal composition provided by the present invention includes, in addition to the first component containing at least one compound represented by the general formula U), and a compound represented by any of the general formulas (2) to (2) depending on the purpose of the liquid crystal composition. 9) Compounds arbitrarily selected from the compound group represented by are mixed and completed.
  • the compounds represented by the general formulas (2) to (4) preferably include the following compounds. (R 3 and Y have the same meanings as described above.)
  • the compounds represented by the general formulas (2) to (4) have a positive dielectric anisotropy value, are excellent in thermal stability and chemical stability, and have a high voltage holding ratio (or a specific resistance). This is a useful compound when preparing a liquid crystal composition for TFT, which requires high reliability (high value).
  • the amount of the compounds represented by the general formulas (2) to (4) depends on the amount of the liquid crystal composition for TFT. When it is prepared, it can be used arbitrarily in the range of 1 to 99% by weight based on the total weight of the liquid crystal composition, but is preferably 10 to 97% by weight, more preferably 40 to 95% by weight. You. In that case, compounds represented by general formulas (7) to (9) may be contained.
  • the compounds represented by the general formulas (2) to (4) can also be used for preparing an STN display mode and a liquid crystal composition for the TN display mode.
  • the compounds represented by the general formulas (5) and (6) have a positive and large dielectric anisotropy value, and are used particularly for the purpose of reducing the threshold voltage. It is also used for adjusting the refractive index anisotropy value and expanding the nematic range such as increasing the clearing point. Furthermore, it is also used for the purpose of improving the steepness of the "transmittance and voltage curves" of the liquid crystal compositions for the STN display method and the TN display method.
  • the compounds represented by the general formulas (5) and (6) are particularly useful when preparing an STN display system and a liquid crystal composition for the TN display system.
  • the amount of the compounds represented by the general formulas (5) and (6) may be in the range of 0.1 to 99.9% by weight when preparing a liquid crystal composition of the STN display mode or the TN display mode. 10-97% by weight, more preferably 40-95% %.
  • the compounds represented by the general formulas (7) to (9) preferably include the following compounds. (R 6 and R 7 have the same meaning as described above.)
  • the compounds represented by the general formulas (7) to (9) have a small absolute value of the dielectric anisotropy and are close to zero.
  • the compound represented by the general formula (7) is mainly used for the purpose of adjusting the viscosity or adjusting the refractive index anisotropy value.
  • the compound represented by) is used for the purpose of extending the nematic range such as increasing the clearing point or adjusting the value of the refractive index anisotropy.
  • the amount of the compounds represented by any of the general formulas (7) to (9) is increased, the viscosity at which the threshold voltage of the liquid crystal composition increases becomes smaller. Therefore, it is desirable to use a large amount as long as the threshold voltage of the liquid crystal composition satisfies the required value.
  • the amount of the compounds represented by the general formulas (7) to (9) is preferably 40% by weight or less, more preferably 35% by weight or less when a liquid crystal composition for a TFT display system is prepared. It is. When preparing a liquid crystal composition for STN display mode or TN display mode, the content is 70% by weight or less, more preferably 60% by weight or less.
  • the necessary twist angle is usually adjusted by inducing a helical structure of the liquid crystal composition.
  • An optically active compound is added for the purpose of preventing reverse twist. Any known optically active compound used for such a purpose can be used in the liquid crystal composition of the present invention. Preferably, the following optically active compounds (Op-l) to (0P- 8).
  • the liquid crystal composition of the present invention generally adjusts the pitch length of the twist by adding these optically active compounds. What is the pitch length of the twist? In the case of a liquid crystal composition for a tablet, it is preferable to adjust the liquid crystal composition to a range of 40 to 200 ⁇ m. If it is a liquid crystal composition for STN, it is preferable to adjust the liquid crystal composition to a range of 6 to 20 m. In the case of the bistable TN (Bistab 1 e TN) mode, it is preferable to adjust the temperature to a range of 1.5 to 4 _ (m. In order to adjust the temperature dependence of the pitch length, Two or more optically active compounds may be added.
  • the liquid crystal composition prepared according to the present invention is prepared by a conventional method. Generally, a method is used in which various components are dissolved at a high temperature.
  • the liquid crystal composition of the present invention may be added to a guest host (GH) by adding a dichroic dye such as a merocyanine-based, styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye. ) It can also be used as a liquid crystal composition for mode.
  • polymer-dispersed liquid crystal display devices such as NCAPs made by microencapsulating nematic liquid crystals and polymer network liquid crystal display devices (PNLCDs) made up of three-dimensional network polymers in liquid crystals. It can also be used as a liquid crystal composition. In addition, it can be used as a liquid crystal composition for birefringence control (ECB) mode and dynamic scattering (DS) mode.
  • ECB birefringence control
  • DS dynamic scattering
  • the compounds represented by the general formula (1) can be obtained from any known literature, for example, the 4th edition Experimental Chemistry Lecture (Maruzen), J. Org. Chem.,, 1821 (1977) ), J. Chem. Soc. Perkin Trans. 2, 2041 (19989).
  • a benzaldehyde derivative (23) is allowed to act on a solution of sodium hydride on ethyl acetyl acetyl phosphonoacetate to obtain a compound (24).
  • the compound (24) is hydrogenated using 0-valent palladium or the like as a catalyst, and the obtained ester derivative (25) is reduced using diisobutylaluminum hydride (hereinafter abbreviated as DI BAL) to obtain an aldehyde derivative (26 ).
  • DI BAL diisobutylaluminum hydride
  • the aldehyde derivative (26) and 2-alkyl-11,3-propanediol are dehydrated in the presence of an acidic catalyst such as para-toluenesulfonic acid (hereinafter abbreviated as PTS) or an acidic ion exchange resin (Amberlyst R). While refluxing, the compound represented by the general formula (1-A) can be obtained.
  • PTS para-toluenesulfonic acid
  • Amberlyst R acidic ion exchange resin
  • Cyclohexanedione monoethylene ketal (28) is allowed to act on the Grignard reagent (27) to give a tertiary alcohol (29). This is dehydrated, hydrogenated and then deprotected under acidic conditions to give the cyclohexanone derivative (31). This is treated with methoxymethyltriphenylphosphonium chloride and then deprotected under acidic conditions to obtain the aldehyde derivative (32).
  • the compound represented by the general formula (1-B) can be obtained by reacting 2-alkyl-1,3-propanediol under acidic conditions.
  • a compound represented by the general formula (1—C) is obtained in the same manner as in the synthesis of the compound represented by the general formula (1—A) except that the aldehyde derivative (23) is replaced with (32). be able to.
  • a compound represented by the general formula (1-D) is obtained in the same manner as in the synthesis of the compound represented by the general formula (1-B) except that the Grignard reagent (27) is replaced by (34). Can be.
  • a compound represented by the general formula U-L) is obtained in the same manner as in the synthesis of the compound represented by the general formula (1-A) except that the aldehyde derivative (23) is replaced by (26). Can be.
  • a compound represented by the general formula (1-M) is obtained in the same manner as in the synthesis of the compound represented by the general formula (1-A) except that the aldehyde derivative (23) is replaced by (33). be able to.
  • the aldehyde derivative (23) was reacted with an aldehyde derivative (23) on an ylide prepared from a base such as 1,3-dioxane-12-ylethyltriphenylphosphonium bromide and potassium 1-butoxide.
  • the product is hydrogenated and deprotected with acid to give the aldehyde derivative (40).
  • the resulting alcohol derivative is brominated with hydrobromic acid or the like to obtain a compound (41), which is then reacted with magnesium to cause a Grignard reagent (42).
  • a compound (43) in which Y is a hydrogen atom in the general formula (1-L) is synthesized.
  • a compound represented by the general formula (1-0) is converted in the same manner as in the synthesis of the compound represented by the general formula (11-E) except that the compound (35) is replaced by (43).
  • Cyclohexanone-4 monoethyl rubynate (50) can be synthesized from pentane-1,3,3,5-tetracarboxylate tetraethyl ester (49) by the following method.
  • methoxymethyltriphenylphosphonium chloride is allowed to act on cyclohexanedione monoethylene ketal, followed by deprotection under acidic conditions to obtain the aldehyde derivative (51). This is oxidized using the method described in Vol. 2, pp. 3-4 of Experimental Chemistry Course, 4th Edition (Maruzen), to give a carboxylic acid derivative (52).
  • the compounds represented by the general formulas (1-F) to U-K) and (1-Q), (1-R), which are four-ring compounds, can be easily produced by utilizing the above-mentioned three-ring compound synthesis method.
  • the compound having a 1-sila 1,4-cyclohexylene group and a 4-sila 1,4-cyclohexylene group may be obtained by applying the method described in Japanese Patent Application Laid-Open No. 7-71048. Can be manufactured.
  • composition examples 1 to 49 can be shown as examples of the liquid crystal composition containing the compound of the present invention.
  • the compounds are shown in the symbol column according to the rules shown in Table 1 below, and the groups shown in the respective columns of the left terminal group, the bonding group, the ring structure, and the right terminal group. I went by making it correspond.
  • the transformer one 1, _4--cyclohexylene and trans is a hydrogen atom hexane one 4, 4 'single Jiiru to trans-bicyclo, J!, Position of J 2, J 3
  • the symbol H [ID, 2D, 3D] is used.
  • the symbol H [5 D, [6 D, 7 D] indicates the deuterium substitution position by the number in [].
  • T N1 nematic isotropic liquid transition temperature or clearing point
  • ⁇ n reffractive index anisotropy: measurement temperature. 2 5. Ot
  • ⁇ ⁇ 1 dielectric anisotropy value: measurement temperature 25.0 ° C
  • V th threshold S threshold voltage: measurement temperature 25.0 ° C. 7
  • 3 -HHB- 1 5.0% 3 -HHB- 39.0% 3 -H2 BTB- 24.0% 3 -H2 BTB- 34.0%
  • V 2 -HB-C 1 0.0% 1
  • V 2 -HB-C 1 0.0% 3 -HB-C 1 1.0% 3 -H [1 D, 2 D, 3 D] BC 9.0%
  • V TH 0.86 (V)
  • V 2 -HHB- 1 1 5.0% 3 -HHB- 19.0% 1 V 2 -HBB- 2 7.0% 3 -HHEBH- 35.0%
  • Composition example 10 3 -D 2 B (F, F) B (F) — OC F 3 0%
  • Composition example 1 4 / JP97 / 02257
  • V th 0.9.8 (V)
  • V th 1.99 (V)
  • V th 1.46 (V)
  • V th 2.25 (V)
  • V 2 7 8 (m P a, s)
  • V 3 3 (m P a )
  • V 21.5 (m P a ⁇ s)
  • V 23.1 (m P a 's)
  • V th 1.83 (V)
  • V th 11.00 33 (V)
  • 3 -HHB- 1 8.0% 3 -HHB-F 4 negligence0% 3— HHB— 0 1 5.0% 3 -HHB- 3 1 4.0% 3 -HHEB-F 4.0% 5 -HHEB -F 4.0%
  • V 2 2 0 (m P as)
  • C represents a crystal
  • SX1 and SX2 each represent a different smectic phase
  • N represents a nematic phase
  • I represents an isotropic liquid phase.
  • the extract was washed with water, saturated aqueous sodium hydrogen carbonate and water in this order, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • 5 g of paratoluenesulfonic acid (abbreviated as TFPTS) and 600 ml of toluene were added to the residue, and the mixture was heated under reflux for 3 hours while removing generated ice using GeneStark.
  • the reaction solution was washed with water, saturated aqueous sodium hydrogen carbonate and water in this order, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

Cette invention concerne des composés de cristaux liquides, lesquels peuvent être utilisés tels quels dans des dispositifs d'affichage à cristaux liquides et à matrice active actionnés par une faible tension. Ces composés possèdent une rétention de tension élevée, ainsi qu'une valeur Δε remarquablement élevée. Ils sont en outre stables sur les plans chimique et électrique, et possèdent une excellente compatibilité avec les composés de cristaux liquides existants. Cette invention concerne également des compositions de cristaux liquides contenant ces composés, ainsi que des dispositifs d'affichage à cristaux liquides fabriqués à l'aide de ces derniers. Les composés susmentionnés consistent en des dérivés de dioxane particuliers qui correspondent à la formule générale (1). Les compositions susmentionnées contiennent un ou plusieurs de ces dérivés.
PCT/JP1997/002257 1996-10-22 1997-06-30 Derives de dioxane, compositions de cristaux liquides contenant ces derives, et dispositif d'affichage a cristaux liquides fabrique a partir de ces derniers WO1998017664A1 (fr)

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EP97928518.6A EP0881221B1 (fr) 1996-10-22 1997-06-30 Derives de dioxane, compositions de cristaux liquides contenant ces derives, et dispositif d'affichage a cristaux liquides fabrique a partir de ces derniers
JP51919698A JP4782255B2 (ja) 1996-10-22 1997-06-30 ジオキサン誘導体、これを含有する液晶組成物、およびこれを用いた液晶表示素子
AU32768/97A AU3276897A (en) 1996-10-22 1997-06-30 Dioxane derivatives, liquid-crystal compositions containing the same, and liquid-crystal display devices made by using the same
US09/101,999 US6235355B1 (en) 1996-10-22 1997-06-30 Dioxane derivatives, liquid-crystal compositions containing the same, and liquid-crystal display devices made by using the same

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JP29798496 1996-10-22
JP8/297984 1996-10-22

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DE19982452B4 (de) * 1998-11-05 2007-09-06 Chisso Corp. Flüssigkristall-Zusammensetzung und ihre Verwendung in einer Flüssigkristall-Anzeigevorrichtung
JP2002193853A (ja) * 2000-12-19 2002-07-10 Merck Patent Gmbh 負のｄｃ異方性の四環式化合物および液晶媒体
JP2004352992A (ja) * 2003-05-27 2004-12-16 Merck Patent Gmbh 液晶媒体
JP2011122154A (ja) * 2003-05-27 2011-06-23 Merck Patent Gmbh 液晶媒体
JP2010106279A (ja) * 2009-12-14 2010-05-13 Chisso Corp 液晶組成物および液晶表示素子
WO2013150826A1 (fr) * 2012-04-02 2013-10-10 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides
JPWO2013150826A1 (ja) * 2012-04-02 2015-12-17 Jnc株式会社 液晶組成物および液晶表示素子
JP2016155772A (ja) * 2015-02-24 2016-09-01 Jnc株式会社 ビニレン基を有する液晶性化合物、液晶組成物および液晶表示素子
WO2017163663A1 (fr) 2016-03-25 2017-09-28 Jnc株式会社 Composition de cristaux liquides et élément d'affichage à cristaux liquides

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JP4782255B2 (ja) 2011-09-28
CN1211978A (zh) 1999-03-24
CN1137116C (zh) 2004-02-04
US6235355B1 (en) 2001-05-22
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EP0881221A1 (fr) 1998-12-02
AU3276897A (en) 1998-05-15

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